The Magnificent Mile
The Mag Mile is one of the most famous shopping areas in the country. With over a mile of stores located just steps from the Loop, the stretch of Michigan Avenue is the perfect stop for anyone looking for an expensive gift for a special someone. As an added bonus, if you go in November, you’ll be able to admire the beautiful holiday lights that adorn the streetlights and buildings.
Andersonville
Like the Magnificent Mile, Clark Street in Andersonville offers a long stretch of stores. Unlike the Mag Mile, Clark Street has a cozier feel, will most definitely not be as crowded as downtown, and stores offer less costly and more unique options. Foursided is an artistic card, poster, and trinket store with an assortment of items for sale. The Brown Elephant is an adventure, not just for the beautiful setting within an old theater, but also for the thrifted clothing, books, and furniture.
The HIP
For something more mainstream than Andersonville but not quite as pricey as the Mag Mile, the Harlem Irving Plaza is an indoor mall on the northwest side that has all your holiday shopping needs. From Hot Topic and Forever 21 to Kohl’s and Target, it’s a great one-stop shop for the busy gift giver. Although it’s located fairly far from the city center, this also means the crowds aren’t nearly as large, making holiday shopping much less stressful.
Wicker Park
This up and coming neighborhood is easy to love, and the long walk along Milwaukee Ave will get you to some truly quirky stores. Transit Tees is a great start for anyone looking to give a gift to a Chicago native, as it carries merchandise for very specific Chicago niches (think parking tickets, El lines, and neighborhoods). The Buffalo Exchange carries retro clothes, and Myopic Books is a one-stop shop for all your reading needs.
Block 37
While the Loop area is close to the Mag Mile, if you’re looking for an indoor option to avoid the cold, Block 37 is there for you. Anthropologie, Sephora, and Zara are located within the sleek building, with easy access from the Blue and Red Lines. You don’t even need to step foot outdoors!
Ukrainian / East Village
For some quintessential neighborhood charm while you shop, you can’t miss Ukrainian Village and its neighbor, East Village. Ukrainian immigrants settled in this part of Chicago in the early 20th century. Most have moved on but the neighborhood retains its distinctive relaxed yet lively energy. Check out RR #1, a gift shop selling wonderfully quirky items in a restored 1930s pharmacy. For the plant lover in your life, Plant Salon is filled with houseplants and everything one needs to grow a green thumb.
